Walter xhopp



Patented July 3, 192s.

UNITED STATES PATENT OFFICE.

WALTER KBOPP, OI ELBEBIELD, GERMANY, ABSIGNORTO WINTHBOP CHEMICAL COI- PANY, INC., 01! NEW YORK, N. Y.

PHARMACEUTICAL COIPOUN D.

' Io Drawing. Application filed September 17, 1925,!erial No. 57,088, and in Germany December 12, 1924.

5 formula:

oo-nnnlon (l) R on 2 1 in which R stands for an alkylene containing more than one carbon atom such as -CH,CH etc., and R stands for an aryl radicle e. g.

ducts which are soluble with difiiculty 'in water. They have proved to be valuable antirheumatlcs and antineuralgics and may be obtained for instance by converting the orthohydroxybenzoic acids or their derivatives by the usual methods into the hydroxyalkylamides, e. g. by treating their esters or halides with aminoa-liphatic alcohols.

In order to illustrate the new process more fully the following example is given, the parts being by wei ht:

75 parts of salicy ic acid methyl ester are 0 heated to 180 C. together withBl parts of aminoethanol in a distillin vessel rovided with a condenser until all 0 the met yl alco-' hol has gone over. To remove the small quantity of the unchanged ester the mass is treated with steam. he new compound crystallizes from water. It is a whitish product melting at 119 C. Its solution is colored violet by a ferric chloride solution. It is easily soluble in alcohol and soluble with more difliculty in ether and has most probably the following formula:

. (IZWNIP-Cflr-CHr-OH a acid methyl ester and aminoethanol crystal- 0-NH--GHr-C Hr-OH on i o I claim:

1. The herein-described new hydroxyalkyl amides of orthohydroxyarylcarboxylic acids having most probably the formula:

wherein R stands for an aryl and'R for an alkylene with more than one carbon atom, which are generally whitish crystalline compounds being soluble with difiiculty in water and being valuable antirheumatics and antineural ics, substantiall as described.

2. T e herein-described hydrox ethylamide of orthohydroxybenzoic acid aving most probably the formula:

which crystallizes from water in the form of whitish cr stals melting at 119 0., beingeasily solu le in alcohol, its aqueous solution being colored violet by a ferric chloride solution, and being a valuable antirheumatic and antineuralgic, substantially as described.

In testimony whereof I ave hereunto set my hand.

WALTER KROPP.

The product obtained from meta-cresotinic 

